4589-33-7

Usage

InChI:InChI=1/C15H11NO5/c1-6-3-7-8(5-16-6)14(19)11-9(17)4-10(21-2)15(20)12(11)13(7)18/h3-5,17,20H,1-2H3

Upstream product

• 73590-03-1 6-hydroxy-7,9-dimethoxy-3-methylbenzoisoquinoline-5,10-quinone 
• 77784-10-2 6,7,9-trimethoxy-3-methylbenzoisoquinoline-5,10-quinone 
• 119975-66-5 anhydrofusarubin lactol 
• 84160-60-1 9-hydroxy-6,7-dimethoxy-3-methylbenzoisoquinoline-5,10-quinone 
• 24011-03-8 3-methylisoquinoline-5,8-dione 
• 77794-86-6 7,9-dimethoxy-3-methylbenzoisoquinoline-5,10-quinone 
• 226717-89-1 3-methyl-6,7,9-trifluorobenzisoquinoline-5,10-dione 

Relevant academic research and scientific papers

General synthetic pathway to oxygenated 3-methylbenz[g]isoquinoline- 5,10-diones

The synthesis of naturally occurring dioxygenated and trioxygenated 3- methylbenz[g]isoquinoline-5,10-diones has been accomplished. The critical step involved regioselective additions of di- or trifluorobenzylzinc bromides to activated methyl 6-methylnicotinate. Aromatizations of the resultant dihydropyridines followed by hydrolysis led to the corresponding benzylpyridinecarboxylic acids which on annulative-oxidations led to the respective difluoro- or trifluorobenz[g]isoquinoline-5,10-diones. Displacements of fluorides by methoxide led to the di- or trimethoxy analogues which on selective demethylations led to bostrycoidin, 8-O- methylbostrycoidin, tolypocladin, 5-deoxybostrycoidin or 5-deoxy-6-O-methyl- bostrycoidin. The synthesis of isobostrycoidin and isotolypocladin has also been accomplished.

5-Deoxybostrycoidin, a New Metabolite Produced by the Fungus Nectria haematococca (Berk. and Br.) Wr.

The structure 2 is established for 5-deoxybostrycoidin, a new metabolite isolated from cultures of the fungus Nectria haematococca (Berk. and Br.) Wr., on the basis of physico-chemical data (MS, 1H and 13C NMR, acetylation) and by reference to the known bostrycoidin 1. - keywords: 5-Deoxybostrycoidin, Fungus, Nectria haematococca, Pigments, Naphthoquinone

Nucleophilic Alkenes. IX Addition of 1,1-Dimethoxyethene to Azanaphthoquinones: Synthesis of Bostrycoidin and 8-O-Methylbostrycoidin

Reaction of 1,1-dimethoxyethene with azanaphthoquinones leads to pairs of isomeric dimethoxyazaanthraquinones by means of 1:2-addition.A photochemical procedure has been developed for substituting these dimethoxy products by a further methoxy, amino or a hydroxy group peri to carbonyl.In this way the antibiotic bostrycoidin (1) and its 8-O-methyl derivative (2), the only natural 2-azaanthraquinone, have been synthesized for the first time.

SYNTHESIS OS BOSTRYCOIDIN AND 8-0-METHYLBOSTRYCOIDIN

The antibiotic bostrycoidin (1) and its 8-O-methyl derivative (2), the only natural 2-azaanthraquinones, have been synthetized for the first time.